Polybasic acid-polyhydric alcohol ether resin and process for preparing same



hailed Mi, 16,1933

UNITED STATES PATENT OFFICE wnm I. LAWSON, or mime-ma, nnmwann, assmnon. r 1*. I. no PONT 1m,

mom & OOIPANY, WILMINGTON, DELAWARE, A CORPORATION 01 DELA- ronmno LO'lD-POLYHYDRIO ALCOHOL ETHER RESIN AND PROCESS BAKE This invention relates to the art of synthetic resins, and more particularly to synthetic resins containing ether groups and compositions made therewith. 5 On account of I the cost and relative scarcity of-natural resins, many attempts have been made to produce synthetic resins, but these attempts have often been unsuc cessful because the resulting resins lacked certain definite properties found to be neceasary for the purposes for which they are intended, such as coating compositions and plastics. Among these properties may be mentioned softness or non-brittleness and compatibility with other materials.

It is an object of this invention to produce synthetic resins which are not brittle.

It is another object of this invention to reduce synthetic resins which are compatible with cellulose derivatives.

It is also an object of this invention to produce compositions of matter containing these resins.

With the above and other objects in view, which will be apparent as the description roceeds, I have set forth below several emiments of my invention by way of illustration and not as a limitation.

Application lied July 87,

FOR PREPARING 192:. Serial No. aaaaar.

phthalic anhydridc, but differ from lyptal resins in containing ether groups, and ave, therefore, a diiferent structure and ossess different properties. On saponi cation with alkali the acid and an ether of an aliphatic polyhydroxy compound containing at least two free hydroxyl groups.

These resins are of value as constituents .of coating compositions. and varnishes, and

Example I Theresin-like materials used in the fol lowing compositions are prepared by heating substantially 1 mol 0 a dibasic acid or its anhydride, such as phthalic anhydride, with 1 mol of a monoalkyl ether of glycerin, such as monoethylin or morwmethylin, at 175-250" C. for 3-14 hours.

In the process of making these resins" the heating may be varied over the range indi cated but the temperature used is that which will insure virtually complete esterification of all the acid and alcohol groups, without being suflicientl high to cause decomposition of either t e reagents or the reaction products.

If desired the acid number of the resin maybe reduced by blowing an inert gas throu h the heated mass to remove any excess thalic anhydride or other acid materi These resins are somewhat similar to the glyptal resins made from glycerol and Part! by weight Cellulose nitrate 15 Monoethylin phthalate 15 Dibutyl phthalate 4.5 Solvent (85% ethyl acetate, 15%

butyl acetate) 100 Eajam-ple 5? Parts by weight Cellulose nitrate 15 Monoethylin succinate 15 Dibutyl phthalate. 4. 5 Solvent (85% ethyl acetate, 15%

butyl acetate) 100 It'wample :3

Parts by weight Ethyl cellulose 8 Monomethylin phthalate 2 Castor oil 4 Solvent (benzene) 100 Although the examples set forth above are limited to the use of resin-like materials formed by using phthalic and succinic acids, it will be understood that other organic acids containing two or more carboxyl grou s may be substituted for phthalic or succinlc acid yieldtne salt of a dibasic for reaction with the monoethylin or monomethylin, or any desired mixtures of these acids may be used for this purpose.

' It will also be apparent that in place of monoethylin or monomethylin I can use ethers of other polyhydroxy com oun'ds, such as other monoalkyl ethers of g ycerin, monoaryl ethers of glycerin, or monoor di-alkyl or aryl ethers of pentaerythrite, mannitol or sorbitoL.

Furthermore, if desired, compositions of thetype set forth herein may also include modifiers of the types generally used in thepreparation oi glyptal resins.

When the resin-like materials are formed from acids containing more than two carboxyl groups and polyhydroxy compounds containing other than two free hydroxyl groups, the relative quantities of these materials employed will usually be varied so that equivalent proportions of the two groups will be present.

However, in making the resin-like materials disclosed herein it is sometimes desirable to vary the proportions of the ingredients and use an excess of one or the other. In such cases, if it'is desired to remove the excess, this may be done in any known way, as by blowing an inert gas through the heated mass.

Cellulose acetate coating compositions containing the resin-like materials disclosed herein are not claimed specifically in this application but are disclosed and claimed in a co-pending application by Frederick O. Hahn, filed of even date herewith.

As many apparently widely different embodiments of this invention may be-made without departing from the spirit thereof, it is tobe understood that I do not limit myself to the foregoing examples, proportions or description except as indicated in the following patent claims.

I claim:

1. The process of forming resin-like materials which consists in heating a hydrocarbon radical ether of a polyhydroxy com pound, said ether containing at least two free hydroxyl groups with an organic acid containing a pluralit of carboxyl roups.

2. The process of orming resin-1i e materials which consists in heating a h drocarbon radical ether of glycerin wit an organic acid containing a plurality of carboxyl groups.

3. The process of forming resin-like materials which consists in heating together an organic acid containing a plurality of carboxyl groups and a monoether of glycerin with an organic compound containing one hydroxyl group.

4. The process of formin resin-like ma terials which consists in heat ng a monoalkyl ether of gl cerin with aniibr' anic. acid containing a p urality oi boxy groups.

5. The rocess of forming resin-like materials whlch consists in heating monoethylin with an organic acid containing a plurality of carboxyl groups.

6. The process of forming resin-like materials which consists" in heating together phthalic acid and a monoether of glycerin with an organic compound containing one hydroxyl group.

7. The process of forming resin-like materials which consists in heating a monoalkyl ether of glycerin with phthalic acid.

8. The process of forming resin-like materials which consists in heating monoethylin with phthalic acid.

9. The process of forming resin-like materials which consists in heating 1 mol oi: monoethylin with 1 mol of phthalic acid at 175250 C. for 3-14 hours.

10. A resinous ester of a hydrocarbon radical ether of a polyhydroxy compound, said ether containing at least two free hydroxyl groups and an organic acid containing a plurality of carboxyl groups.

11. A resinous ester of a hydrocarbon radical ether of glycerin and an organic acid 1 ontaining a plurality of carboxyl groups.

12. A resinous ester of a monocthcr ot' glycerin with an organic compound contain ing one hydroxyl group and an organic acid containing a plurality of carboxyl groups.

1.3. A resinous ester of a monoalkyl other i of glycerin and an organic acid containing a plurality of carboxyl groups.

14. A resinous ester of monoethylin and an organic acid containing a plurality of carboxyl groups.

15. As a, new resin-like product, a phthalate of a hydrocarbon radical ether of a polyhydroxy'compound, said ether containing at least two free hydroxyl groups.

16. As a new resin-like product, a phthalate of a hydrocarbon radical ether of glycerin.

17. As a new resin-like product, a phthalate of monoethylin.

In testimony whereof, Iafiix my signature.

WALTER E. LAWSON. 

